An Efficient Synthesis of Fused 2‐Aryliminothiazolines via a Solvent‐Free Cyclopropyliminium Rearrangement

An Efficient Synthesis of Fused 2‐Aryliminothiazolines via a Solvent‐Free Cyclopropyliminium Rearrangement Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2016, Volume: 1, Number: 10, Pages: 2373-2376 Pages count : 4 DOI: 10.1002/slct.201600453

Authors

Samet Alexander V. ¹ , Silyanova Evgenia A. ¹ , Semenova Marina N. ² , Karnoukhova Valentina A. ³ , Semenov Victor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Pr., 119991 Moscow, Russia
2	N. K. Kolt'sov Institute of Developmental Biology, Russian Academy of Sciences, 26 Vavilov Str., 119334 Moscow, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., 119991 Moscow, Russia.

(Z)-3-Aryliminopyrrolo[1,2-c]thiazoles were prepared by a base-induced dehydrobromination of 3-arylaminopyrrolo[1,2-c]thiazolium bromides, which, in turn, were obtained via an efficient solvent-free cyclopropyliminium rearrangement of the corresponding 4-cyclopropylthiazole hydrobromides proceeding in melt at high rate and in excellent yields. Biological evaluation using phenotypic sea urchin embryo assay showed that 2-arylamino-4-cyclopropylthiazoles displayed an antimitotic tubulin-unrelated activity, whereas fused-ring rearrangement products were proposed to inhibit Ca-Zn–dependent metalloproteases.

Samet A.V. , Silyanova E.A. , Semenova M.N. , Karnoukhova V.A. , Semenov V.V.
An Efficient Synthesis of Fused 2‐Aryliminothiazolines via a Solvent‐Free Cyclopropyliminium Rearrangement
ChemistrySelect. 2016. V.1. N10. P.2373-2376. DOI: 10.1002/slct.201600453 WOS Scopus OpenAlex

Web of science:	WOS:000395417800041
Scopus:	2-s2.0-85041958276
OpenAlex:	W2460721912

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OpenAlex	2
Scopus	1
Web of science	1